PMT

Please check the examination details below before entering your candidate information
Candidate surname Other names

Pearson Edexcel Centre Number Candidate Number

International
Advanced Level

Tuesday 2 June 2020

Afternoon (Time: 1 hour 45 minutes) Paper Reference WCH14/01

Chemistry
International Advanced Level
Unit 4: Rates, Equilibria and Further Organic Chemistry

Candidates must have: Scientific calculator Total Marks

Data Booklet
Ruler

Instructions
• Use black ink or black ball-point pen.
• centre
Fill in the boxes at the top of this page with your name,
number and candidate number.
• Answer allthequestions.
Answer
• – there may bequestions in the spaces provided
more space than you need.

Information
• The total mark for this paper is 90.
• The marks for each question are shown in brackets
– use this as a guide as to how much time to spend on each question.
• ability
In the question marked with an asterisk (*), marks will be awarded for your
to structure your answer logically, showing how the points that you make
are related or follow on from each other where appropriate.
• A Periodic Table is printed on the back cover of this paper.

Advice
• Read each question carefully before you start to answer it.
• Checkyour
Show working in calculations and include units where appropriate.
• your answers if you have time at the end.
Turn over

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SECTION A
Answer ALL the questions in this section.
You should aim to spend no more than 20 minutes on this section.
For each question, select one answer from A to D and put a cross in the box . If you change
your mind, put a line through the box and then mark your new answer with a cross .
1 Bromine oxidises methanoic acid to carbon dioxide.
The equation for the reaction is

HCOOH(aq) + Br2(aq) → 2H+(aq) + 2Br −(aq) + CO2(g)

Which of the following methods would not be suitable for measuring the progress of
this reaction?
A colorimetry
B measuring electrical conductivity
C quenching and titrating with acid
D measuring the volume of gas
(Total for Question 1 = 1 mark)
Use this space for any rough working. Anything you write in this space will gain no credit.

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2 The rate of the reaction between two compounds, Y and Z, was investigated.
The results are shown.

Initial concentration of Y Initial concentration of Z Initial rate

Experiment
/ mol dm−3 / mol dm−3 / mol dm−3 s−1
1 0.64 0.24 8.00 × 10−3

2 0.64 0.48 3.20 × 10−2

3 0.32 0.48 3.20 × 10−2

What are the orders of reaction with respect to Y and Z?

Order with respect to Y Order with respect to Z

A 0 1

B 0 2

C 1 1

D 1 2

(Total for Question 2 = 1 mark)

Use this space for any rough working. Anything you write in this space will gain no credit.

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3 The inorganic anti-cancer drug cis-platin, Pt(NH3)2Cl2, is hydrolysed by water to make

it active. The reaction is
+
H3N NH3 H3N NH3
Pt + H2O Pt + Cl−
Cl Cl H2O Cl

The hydrolysis is first order overall. The half-life can be found from a graph of the
concentration of cis-platin against time.

20

18

16

14

12

Concentration of
cis-platin × 10−3 10
/ mol dm−3
8

0
0 200 400 600 800 1000 1200
Time of reaction / min

The half-life of the reaction is

A 430 min
B 460 min
C 590 min
D 600 min

(Total for Question 3 = 1 mark)

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4 Propanone reacts with iodine in acidic solution.

CH3COCH3(aq) + I2(aq) → CH3COCH2I(aq) + H+(aq) + I−(aq)

The rate equation for the formation of iodopropanone is found to be

rate = k[CH3COCH3(aq)][H+(aq)]

(a) Which of the following is true?

(1)

A the units for the rate constant are dm3 mol−1 s−1
B the reaction is a first order reaction overall
C the units for the rate are dm3 mol −1 s−1
D doubling the concentrations of propanone and of iodine quadruples the rate

(b) Which of the following is not true?

(1)

A the reaction rate increases if the temperature is raised

B the rate constant increases if the temperature is raised
C the addition of a small amount of sodium hydroxide decreases the
reaction rate
D the rate is unchanged when the hydrogen ion concentration is doubled

(Total for Question 4 = 2 marks)

Use this space for any rough working. Anything you write in this space will gain no credit.

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5 The equation shows the hydrolysis of a bromoalkane.

RBr + OH− → ROH + Br−

The rate equation is rate = k[RBr]

RBr is most likely to be

A bromomethane
B 2-bromopropane
C 1-bromo-2-methylpropane
D 2-bromo-2-methylpropane

(Total for Question 5 = 1 mark)

6 The equation for an exothermic reaction is shown.

Mg(s) + 2HCl(aq) → MgCl2(aq) + H2(g)

Which of these is true?

A ΔH is positive
B ΔSsurroundings is positive
C ΔSsystem is negative
D ΔStotal is negative

(Total for Question 6 = 1 mark)

Use this space for any rough working. Anything you write in this space will gain no credit.

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7 The equation for the equilibrium decomposition of hydrogen iodide into hydrogen
and iodine can be written in two ways.
2HI(g)  H2(g) + I2(g) Equilibrium constant = Kc
or
HI(g)  ½H2(g) + ½I2(g) Equilibrium constant = Kcʹ
What is the expression linking the two equilibrium constants?
A Kc = (Kcʹ )2
B Kc = Kcʹ
C Kc = 2(Kcʹ )
D Kc = K ¢c

(Total for Question 7 = 1 mark)

8 A buffer solution contains ethanoic acid, with a concentration of 0.10 mol dm−3, and
sodium ethanoate, with a concentration of 0.050 mol dm−3.
Ka for ethanoic acid = 1.7 × 10−5 mol dm−3
The pH of this buffer solution is
A 2.88

B 4.47

C 4.77

D 5.07

(Total for Question 8 = 1 mark)

Use this space for any rough working. Anything you write in this space will gain no credit.

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9 The graphs show the changes in pH during a series of titrations.

Each titration involves two solutions, each of concentration 0.1 mol dm−3.

Graph 1 Graph 2

14 14
12 12
10 10
8 8
pH pH
6 6
4 4
2 2
0 0
0 10 20 30 40 0 10 20 30 40
Volume of solution added / cm3 Volume of solution added / cm3

Graph 3 Graph 4

14 14
12 12
10 10
8 8
pH pH
6 6
4 4
2 2
0 0
0 10 20 30 40 0 10 20 30 40
Volume of solution added / cm3 Volume of solution added / cm3

(a) Which graph has ethanoic acid as one of the reactants?

(1)
A Graph 1
B Graph 2
C Graph 3
D Graph 4

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(b) Which graph shows a solution that has an acidic pH at the end-point?
(1)
A Graph 1
B Graph 2
C Graph 3
D Graph 4

(c) Which indicator is suitable for the titration shown in Graph 3?

Use your Data Booklet.
(1)
A bromocresol green
B bromothymol blue
C phenol red
D thymol blue (acid)

(Total for Question 9 = 3 marks)

Use this space for any rough working. Anything you write in this space will gain no credit.

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10 Which diagram shows the first step of the mechanism for the nucleophilic addition of
hydrogen cyanide to propanone in the presence of potassium cyanide?
δ−
O
δ+ O–

••
C
A H3C CH3 H3C C CH3
CN− CN

••
δ−
O
δ+ O–

••
C
B H3C CH3 H3C C CH3
CN− CN
••

δ+
O
δ− O–
••

C
C H3C CH3 H3C C CH3
−
CN CN
••

δ−
O
δ+ O–
••

C
D H3C CH3 H3C C CH3
−
CN CN
••

(Total for Question 10 = 1 mark)

Use this space for any rough working. Anything you write in this space will gain no credit.

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11 When propanone reacts with iodine in the presence of sodium hydroxide, the
precipitate formed has the formula
A CH3I
B CHI3
C CH3COCH2I
D CH3COCI3

(Total for Question 11 = 1 mark)

12 Which of the following could not be formed when methylamine is added to

ethanoyl chloride?
A HCl
B CH3NH3+Cl−
C CH3CONH2
D CH3CONHCH3

(Total for Question 12 = 1 mark)

13 In which of these esters is the percentage by mass of carbon 54.5 %?

A methyl methanoate, HCOOCH3
B methyl ethanoate, CH3COOCH3
C ethyl ethanoate, CH3COOCH2CH3
D ethyl methanoate, HCOOCH2CH3

(Total for Question 13 = 1 mark)

14 An organic compound that reacts with both lithium tetrahydridoaluminate(III)

(lithium aluminium hydride) and magnesium could be
A an aldehyde
B a carboxylic acid
C a ketone
D a tertiary alcohol

(Total for Question 14 = 1 mark)

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15 The following methods can be used to distinguish between pairs of organic compounds
with no further tests.
A warm each compound with Fehling’s or Benedict’s solution
B warm each compound with acidified potassium dichromate(VI) solution
C add 2,4-dinitrophenylhydrazine (Brady’s reagent) to each compound
D add a few drops of each compound, drop by drop, to water

(a) Which test would distinguish between 2-methylpropan-2-ol, (CH3)3COH, and

butanone, CH3CH2COCH3?
(1)
A
B
C
D

(b) Which test would distinguish between 2-methylpropan-2-ol, (CH3)3COH, and

butan-1-ol, CH3CH2CH2CH2OH?
(1)
A
B
C
D

(c) Which test could not be used to distinguish between 2-methylpropan-2-ol,

(CH3)3COH, and butanal, CH3CH2CH2CHO?
(1)
A
B
C
D

(Total for Question 15 = 3 marks)

TOTAL FOR SECTION A = 20 MARKS

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BLANK PAGE

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SECTION B
Answer ALL the questions. Write your answers in the spaces provided.
16 This question concerns calcium chloride, CaCl2 .
(a) Some energy changes related to calcium chloride are shown.

Energy change Value / kJ mol−1

Atomisation energy of calcium +178.2

Atomisation energy of chlorine +121.7

Electron affinity of chlorine −348.8

First ionisation energy of calcium +590.0

Standard enthalpy change of formation of calcium chloride −795.8

Experimental lattice energy of calcium chloride −2 258

Second ionisation energy of calcium To be calculated

(i) Complete the Born-Haber cycle by writing appropriate chemical formulae on

the horizontal lines. Include state symbols and relevant electrons.
(4)

∆H5 ∆H6

Ca2+(g) + 2Cl−(g)
∆H4

∆H3

∆H7
∆H2
Ca(s) + Cl2(g)

∆H1
CaCl2(s)

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(ii) Calculate the second ionisation energy of calcium using the cycle and the
values given in the table. Include a sign and units with your value.
(3)

(b) The theoretical lattice energy of formation of CaCl2 is −2 223 kJ mol−1.

Explain why the experimental lattice energy of CaCl2 is more exothermic than the
theoretical value.
(3)

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(c) The table shows the theoretical lattice energies of some chlorides of Group 2.

magnesium calcium strontium barium

Group 2 metal chloride
chloride chloride chloride chloride

Lattice energy / kJ mol−1 −2 326 −2 223 −2 127 −2 033

Explain the trend in theoretical lattice energies on descending Group 2.

(3)

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(d) Calculate the enthalpy change of solution of calcium chloride, CaCl2.

Data

∆hyd H (Ca2+) = −1 650 kJ mol−1 ∆hyd H (Cl−) = −364 kJ mol−1

Experimental lattice energy (CaCl2) = −2 258 kJ mol−1
(2)

(Total for Question 16 = 15 marks)

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17 This question concerns six isomers each with the molecular formula C5H10O2.
(a) Isomers A, B, C and D are structural isomers that all react with aqueous sodium carbonate
to produce carbon dioxide.
Isomer A is a straight-chain compound.
Isomer B has only two peaks in its high resolution proton NMR spectrum, both of
which are singlets.
Isomer C contains a chiral centre but isomer D does not.
Give the structures of these four isomers.
(4)

A B

C D

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(b) (i) Isomer E contains an ether functional group (R-O-R) and a ketone functional
group. The low resolution proton NMR spectrum of isomer E has four peaks.
The displayed formula of isomer E is

O
CH3 O CH2 CH2 C CH3
a b c d

The four hydrogen environments responsible for the four peaks are labelled.
Complete the table of information regarding these peaks including the
splitting pattern in the high resolution spectrum.
(3)

Peak a b c d

Relative peak area 3

Chemical shift
2.9 − 4.2
range, δ / ppm

Splitting singlet

(ii) State the number of peaks in the carbon-13 (13C) NMR spectrum of E.
(1)

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(c) Isomer F is a neutral compound that smells of pears.

It can be formed by the reaction between compounds V and W in the presence
of concentrated sulfuric acid.
Compound V has an absorption in its infrared spectrum at 1720 cm−1 and a
broad absorption around 3050 cm−1.
Compound W can be formed directly from propanal.
(i) Identify, by name or formula, compounds V, W and F.
Justify your answer by using all the available information.
(4)

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(ii) State the conditions required and the reagent needed to form compound W
from propanal.
(1)

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(iii) State the role of sulfuric acid in the formation of F.

(1)

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(d) State which one of the isomers A, E and F has the highest boiling temperature.
Justify your answer.
(3)

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(Total for Question 17 = 17 marks)

20
*P64620A02032*
 PMT

18 This question concerns acidic solutions.

(a) (i) A solution of hydrochloric acid has a pH of 1.125.
Calculate the concentration of hydrogen ions and of hydroxide ions, in mol dm−3,
in this solution.
[Kw = 1.00 × 10−14 mol2 dm−6]
(2)

(ii) Calculate the volume of water which must be added to 25.0 cm3 of this
solution to increase the pH from 1.125 to 1.500, giving your answer to an
appropriate number of significant figures.
(4)

21
*P64620A02132* Turn over
 PMT

(b) Phosphoric(V) acid, H3PO4 , is a weak acid, which dissolves in water, giving the
equilibrium

Equation 1 H3PO4(aq) + H2O(l)  H2PO4− (aq) + H3O+(aq)

The H2PO4− ion formed when phosphoric(V) acid is added to water can dissociate
further into HPO2−
4 .

Equation 2 H2PO4− (aq) + H2O(l)  HPO2−

4 (aq) + H3O+(aq)

.................... .................... .................... ....................

(i) Identify the acids and bases in the spaces below Equation 2, linking the
acid-base conjugate pairs.
(2)
(ii) Explain why very little dissociation of the H2PO4− ion occurs in solutions of
phosphoric(V) acid.
(2)

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22
*P64620A02232*
 PMT

(c) (i) Using Equation 1, write an expression for the acid dissociation constant, Ka1 ,
for phosphoric(V) acid, H3PO4 .
(1)

(ii) A 0.500 mol dm−3 solution of phosphoric(V) acid has a pH of 1.20.

Calculate the value of Ka1 , stating its units.
Assume that there is no further dissociation of the H2PO4− ion.
(4)

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*P64620A02332* Turn over
 PMT

(d) Phosphate buffer solutions containing hydrogenphosphate ions, HPO2−4 , and

−
dihydrogenphosphate ions, H2PO4 , are commonly used in biological research.
Explain, using a relevant ionic equation, how a solution containing these ions can
act as a buffer when a small amount of alkali is added.
(3)

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(Total for Question 18 = 18 marks)

TOTAL FOR SECTION B = 50 MARKS

24
*P64620A02432*
 PMT

BLANK PAGE

25
*P64620A02532* Turn over
 PMT

SECTION C
Answer ALL the questions. Write your answers in the spaces provided.
19 Ammonia is manufactured in the Haber Process.

N2(g) + 3H2(g)  2NH3(g)

In this process, pressures between 100 atm and 300 atm and temperatures between
675 K and 725 K are usually used.
(a) (i) Calculate ∆Ssystem for this reaction at 298 K.
Include a sign and units with your answer.
[Standard molar entropy, S , for 1 mol of each gas, in J K−1 mol−1 :
N2 = 191.6 H2 = 130.6 NH3 = 192.3]
(2)

(ii) Explain, using ideas about disorder, whether the sign of your answer to (a)(i) is
as expected.
(2)

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26
*P64620A02632*
 PMT

(iii) At 700 K, the enthalpy change for this reaction is ∆H = −110.2 kJ mol−1.
Calculate the entropy change of the surroundings, ∆Ssurroundings , at 700 K.
Include a sign and units in your answer.
(2)

(iv) At 700 K, the total entropy change, ∆Stotal = −78.7 J K−1 mol−1.
Calculate ∆Ssystem for this reaction at 700 K.
Include a sign and units in your answer.
(1)

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*P64620A02732* Turn over
 PMT

*(v) Explain one advantage and one disadvantage of using a temperature higher
than 700 K in the Haber process.
Consider the effect of an increase in temperature on the rate of reaction, on the
values of ∆Ssurroundings and ∆Stotal and on the equilibrium constant.
(6)

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28
*P64620A02832*
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

29
*P64620A02932* Turn over
 PMT

(b) (i) Write the expression for the equilibrium constant, Kp , for the reaction in the
Haber Process.

N2(g) + 3H2(g)  2NH3(g)

(1)

(ii) A mixture of nitrogen, hydrogen and ammonia is at equilibrium at 255 atm

and 700 K. The partial pressure of nitrogen is 25 atm and that of hydrogen is
150 atm.
Calculate the equilibrium constant, Kp , for the formation of ammonia, at 700 K.
Include units in your answer.
(3)

30
*P64620A03032*
 PMT

(iii) The pressure of the system is doubled at constant temperature.

Explain the effect of this on the yield of ammonia by considering the change
in the Kp expression and hence the position of equilibrium.
(3)

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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(Total for Question 19 = 20 marks)

TOTAL FOR SECTION C = 20 MARKS

TOTAL FOR PAPER = 90 MARKS

31
*P64620A03132*
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32
*P64620A03232*